Amino acid grafted polymer with soot handling properties

Abstract

The present disclosure relates to lubricant additives such as dispersants and dispersant viscosity modifiers including acyl peptide grafted polymers and lubricating oil compositions comprising such additives. The disclosure also relates to the use of lubricant compositions comprising the additives herein for improving the soot or sludge handling characteristics of an engine lubricant composition and while minimizing the deterioration of engine's elastomer compatibility.

What is claimed is: 
     
       1. A multi-functional olefin copolymer lubricant additive comprising a reaction product of an acylated olefin copolymer and an amino mono- or di-carboxylic acid, and wherein the amino mono- or di-carboxylic acid has the formula
   H 2 N—R 1 (R 2 )—COOH
 
 
       wherein
 R 1  is a C1 to C18 hydrocarbyl group; 
 R 2  is hydrogen, a linear or branched alkyl group, an aryl group, a hydroxyphenyl group, a heterocyclic amino group, a carboxyl group, an amido group, an amino group, a hydroxyl group, a thiol, a thioester, selenium, or combinations thereof; and 
 wherein the acylated olefin copolymer is derived from a copolymer of ethylene and one or more C3 to C18 alpha-olefins and a grafted ethylenically unsaturated carboxylic acid material selected from acrylic acid, methacrylate acid, cinnamic acid, crotonic acid, maleic acid, fumaric acid or anhydride derivatives thereof. 
 
     
     
       2. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and the amine, ester, or alcohol functionalization agent is selected from aromatic amines, polyaromatic amines, primary amines, secondary amines, primary or secondary alcohols, napthyl alkyl amines, and mixtures thereof. 
     
     
       3. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is formed in either the L or D isomeric form. 
     
     
       4. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is either neutral or ionic. 
     
     
       5. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the acylated olefin copolymer includes an olefin copolymer having grafted thereon from 0.1 to 0.8 carboxylic groups per 1000 number average molecular weight units of the olefin copolymer. 
     
     
       6. The multi-functional olefin copolymer lubricant additive of  claim 5 , wherein the olefin copolymer has a number average molecular weight between about 5,000 and about 200,000 as measured by GPC using polystyrene as reference. 
     
     
       7. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein R 1  is a methylene group and R 2  is the heterocyclic amino group selected from an indole alkyl group or an imidazole alkyl group. 
     
     
       8. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the amino mono- or di-carboxylic acid is selected from amino hexanoic acid, 2-amino-3-phenyl propanoic acid, 2-amino-3-(1H-indol-3-yl) propanoic acid, 2-amino-3-(1H-imidazol-5-yl) propanoic acid, 2-amino butane dioic acid, 2-amino pentane dioic acid, 2-amino-4-methylpentanoic acid, and mixtures thereof. 
     
     
       9. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and wherein a primary or secondary amine thereof is capped with an oxazoline or derivative thereof. 
     
     
       10. The multi-functional olefin copolymer lubricant additive of  claim 9 , wherein the oxazoline or derivative thereof is 2-phenyl-2-oxazoline; 2-ethyl-2 oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2 oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2,4,5-trimethyl-3-oxazoline; dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-[1-(hydroxymethyl)ethyl] oxazoline; mixtures thereof, or derivatives thereof. 
     
     
       11. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and wherein the amine functionalization agent is selected from N-arylphenylene-diamine, 1-(2-amino-ethyl)-imidazolidin-2-one, N-(3-aminopropyl) morpholine, 3-(dimethylamino)-1-propylamine, N-phenyl-p-phenylenediamine, N-(3-aminopropyl)-2 pyrrolidinone, aminoethylacetamide, alanine methyl ester, 1-(3-aminopropyl) imidazole, polyetheramine, phenoxypropylamine, aromatic derivatives thereof, and combinations thereof. 
     
     
       12. The multi-functional olefin copolymer lubricant additive of  claim 11 , wherein the amine functionalization agent is an N arylphenylenediamine of the formula 
       
         
           
           
               
               
           
         
       
       wherein R 4  is hydrogen, —NH-aryl, —NH-arylalkyl, —NH-alkyl, or a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl aralkyl, alkaryl, hydroxyalkyl or aminoalkyl; R 5  is —NH 2 , CH 2 —(CH 2 ), —NH 2 , or CH 2 -aryl-NH 2 , in which n is an integer from 1 to 10; and R 6  is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, or alkaryl having from 4 to 24 carbon atoms. 
     
     
       13. The multi-functional olefin copolymer lubricant additive of  claim 12 , wherein the N arylphenylenediamine is selected from N-phenyl-1,4-phenylenediamine; N-phenyl-1,3-phenyl endi amine; N-phenyl-1,2-phenylenediamine; and mixtures thereof. 
     
     
       14. A lubricant composition comprising:
 a major amount of base oil of lubricating viscosity; and 
 a multi-functional olefin copolymer viscosity modifier comprising a reaction product of an acylated olefin copolymer and an amino mono- or di-carboxylic acid, and wherein the amino mono- or di-carboxylic acid has the formula
   H 2 N—R 1 (R 2 )—COOH
 
 
 
       wherein
 R 1  is a C1 to C18 hydrocarbyl group; 
 R 2  is hydrogen, a linear or branched alkyl group, an aryl group, a hydroxyphenyl group, a heterocyclic amino group, a carboxyl group, an amido group, an amino group, a hydroxyl group, a thiol, a thioester, selenium, or combinations thereof; and 
 wherein the acylated olefin copolymer is derived from a copolymer of ethylene and one or more C3 to C18 alpha-olefins and a grafted ethylenically unsaturated carboxylic acid material selected from acrylic acid, methacrylate acid, cinnamic acid, crotonic acid, maleic acid, fumaric acid or anhydride derivatives thereof. 
 
     
     
       15. The lubricant composition of  claim 14 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and the amine, ester, or alcohol functionalization agent is selected from aromatic amines, polyaromatic amines, primary amines, secondary amines, primary or secondary alcohols, napthyl alkyl amines, and mixtures thereof. 
     
     
       16. The lubricant composition of  claim 14 , wherein the reaction product is formed in either the L or D isomeric form. 
     
     
       17. The lubricant composition of  claim 14 , wherein the reaction product is either neutral or ionic. 
     
     
       18. The lubricant composition of  claim 14 , wherein the acylated olefin copolymer includes an olefin copolymer having grafted thereon from 0.1 to 0.8 carboxylic groups per 1000 number average molecular weight units of the olefin copolymer. 
     
     
       19. The lubricant composition of  claim 18 , wherein the olefin copolymer has a number average molecular weight between about 5,000 and about 200,000 as measured by GPC using polystyrene as reference. 
     
     
       20. The lubricant composition of  claim 14 , wherein R 1  is a methylene group and R 2  is the heterocyclic amino group selected from an indole alkyl group or an imidazole alkyl group. 
     
     
       21. The lubricant composition of  claim 14 , wherein the amino mono- or di-carboxylic acid is selected from amino hexanoic acid, 2-amino-3-phenyl propanoic acid, 2-amino-3-(1H-indol-3-yl) propanoic acid, 2-amino-3-(1H-imidazol-5-yl) propanoic acid, 2-amino butane dioic acid, 2-amino pentane dioic acid, 2-amino-4-methylpentanoic acid, and mixtures thereof. 
     
     
       22. The lubricant composition of  claim 14 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and wherein a primary or secondary amine thereof is capped with an oxazoline or derivative thereof. 
     
     
       23. The lubricant composition of  claim 22 , wherein the oxazoline or derivative thereof is 2-phenyl-2-oxazoline; 2-ethyl-2 oxazoline; 2-methyl-2-oxazoline; 2-benzyl-4,4-dimethyl-2-oxazoline; 2-ethyl-4,4-dimethyl-2 oxazoline; 2,4,4-trimethyl-2-oxazoline; 4,4-dimethyl-2-oxazoline; 2,4,5-trimethyl-3-oxazoline; 2-(2,6-dimethoxyphenyl)-4,4-dimethyl-2-oxazoline; 2-[1-(hydroxymethyl)ethyl] oxazoline; mixtures thereof, or derivatives thereof. 
     
     
       24. The lubricant composition of  claim 14 , wherein the reaction product is further reacted with an amine, ester, or alcohol functionalization agent, and wherein the amine functionalization agent is selected from N-arylphenylene-diamine, 1-(2-amino-ethyl)-imidazolidin-2-one, N-(3-aminopropyl) morpholine, 3-(dimethylamino)-1-propylamine, N-phenyl-p-phenylenediamine, N-(3-aminopropyl)-2 pyrrolidinone, aminoethylacetamide, alanine methyl ester, 1-(3-aminopropyl) imidazole, polyetheramine, phenoxypropylamine, aromatic derivatives thereof, and combinations thereof. 
     
     
       25. The lubricant composition of  claim 24 , wherein the amine functionalization agent is an N arylphenylenediamine of the formula 
       
         
           
           
               
               
           
         
       
       wherein R 4  is hydrogen, —NH-aryl, —NH-arylalkyl, —NH-alkyl, or a branched or straight chain radical having from 4 to 24 carbon atoms that can be alkyl, alkenyl, alkoxyl aralkyl, alkaryl, hydroxyalkyl or aminoalkyl; R 5  is —NH 2 , CH 2 —(CH 2 ), —NH 2 , or CH 2 -aryl-NH 2 , in which n is an integer from 1 to 10; and R 6  is hydrogen, alkyl, alkenyl, alkoxyl, aralkyl, or alkaryl having from 4 to 24 carbon atoms. 
     
     
       26. The lubricant composition of  claim 25 , wherein the N-arylphenylenediamine is selected from N-phenyl-1,4-phenylenediamine; N-phenyl-1,3-phenylendiamine; N-phenyl-1,2-phenylenediamine; and mixtures thereof. 
     
     
       27. The multi-functional olefin copolymer lubricant additive of  claim 1 , wherein the reaction product is an olefin copolymer with grafted carboxylic acid substituted succinimide moieties thereon. 
     
     
       28. The lubricant composition of  claim 14 , wherein the reaction product is an olefin copolymer with grafted carboxylic acid substituted succinimide moieties thereon.